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Biography: James Montgomery Flagg (1877-1960) was born in Pelham Manor, New York. Talented in art as a youth, he successfully submitted illustrations to the children's magazine St. Nicholas when he was twelve. Three years later, he was a staff artist for Life and Judge magazines. From 1894 through 1898, he attended the Art Students League of New York. After studies in London and Paris from 1898–1900, he returned to the United States, where he created illustrations for books, magazines, political and humorous cartoons, and advertisements over his long career. His work appeared in leading magazines, including The Saturday Evening Post, Photoplay, McClure's, Cosmopolitan, Redbook, Liberty, Collier's, Women's Home Companion, and the Ladies' Home Journal.

Especially skilled in pen and ink, Flagg was a master of many media, which contributed to the facility and speed of his numerous commissions. He also painted portraits of well-known subjects, including John Singer Sargent, Mark Twain, and Ethel Barrymore.

His most famous work remains a 1917 recruitment poster for the United States Army during World War I, featuring an image of Uncle Sam, a traditional personification of the American government, pointing at the viewer with the caption "I Want YOU for U.S. Army". Inspired by British artist Alfred Leete's poster showing Lord Kitchener in a similar pose, the image generated over four million copies; it was revived for World War II. From 1917 to 1919, as a member of the government's Division of Pictorial Publicity, Flagg designed 46 American war posters.

In 1899 Flagg married Nellie McCormick, a wealthy St. Louis socialite. They maintained homes in California, Florida, and Virginia. Upon her death in 1923, he married his model Dorothy Virginia Wadman; their daughter Faith was born in 1925.